The goal of the proposed research is to discover and develop practical methods for the asymmetric oxidation of organic compounds. In spite of great current interest in asymmetric synthesis, little has been achieved in the area of asymmetric oxidations. Our initial efforts will be with olefins since no other functional group is as susceptible to such a wide variety of useful oxidative transformations. Epoxidation is the single most important oxidative process for olefins, and thus will receive special attention. Our approach is to devise chiral metal catalysts and thereby realize high enantioselectivities in the same manner that enzymes do. The principal challenge is the synthesis of special chiral ligands for the metals (e.g. vanadium, molybdenum, osmium and selenium) which are active as oxidation catalysts. We are encouraged by our recent achievement of good (80% e.e.) inductions in epoxidations using chiral vanadium catalysts. We have also discovered the first asymmetric examples of other important oxidative transformations of olefins (e.g. allylic oxygenation, allylic amination and vicinal oxyamination). We hope to develop a variety of oxidative methods for the introdution of oxygen and nitrogen into organic molecules with good yields and high optical purity. Most biologically active molecules are optically active and contain oxygen and nitrogen. Therefore, the proposed research offers the promise of facilitating the syntheses of many drugs and vitamins.